I think we consider it a trailerable boat, not a trailer sailor. We normally set aside a day for rigging up the mast & rigging & sails. It may take us less, but we do not rush things. Often, we take a few days longer just to explore around the area. Took us a month to rig when we were in New Orleans for Mardi Gras!
The GREAT part is it's very low cost to keep here close to us here in Az. we will trail her to Fla. in a couple of months and spend 4 to 6 months cruising, VERY comfortably. Then put back in storage for the hurricane season.
BUT, ya got to chose the right boat for what you want to do! Get on the water fast and do weekending or spend more time and go further.
Greg